3-(1,2-Di-p-tolyl­vin­yl)-2-methyl-1H-indole

Senthamizhselvi, R.; Bhaskar, G.; Seshadri, P.R.; Perumal, P.T.; Illangovan, K.

doi:10.1107/S1600536812021617

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1815

doi:10.1107/S1600536812021617

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3-(1,2-Di-p-tolylvinyl)-2-methyl-1H-indole

R. Senthamizhselvi,^a G. Bhaskar,^b P. R. Seshadri,^c ^* P. T. Perumal ^b and K. Illangovan ^d

^aDepartment of Chemistry, Easwari Engineering College, Ramapuram, Chennai 600 089, India, ^bOrganic Chemistry Division, Central Leather Research Institute, Chennai 600 020, India, ^cPost Graduate and Research Department of Physics, Agurchand Manmull Jain College, Chennai 600 114, India, and ^dPost Graduate and Research Department of Physics, RKM Vivekananda College, Chennai 600 004, India
^*Correspondence e-mail: seshadri_pr@yahoo.com

(Received 6 May 2012; accepted 13 May 2012; online 19 May 2012)

In the title compound, C₂₅H₂₃N, the indole unit makes a dihedral angles of 79.03 (5) and 61.82 (4)° with the benzene rings. No classical hydrogen bonds are found in the crystal structure.

Related literature

For the biological activity of indole derivatives, see: Olgen & Coban (2003 ); Joshi & Chand (1982 ).

Experimental

Crystal data

C₂₅H₂₃N
M_r = 337.44
Monoclinic, C 2/c
a = 25.684 (6) Å
b = 9.911 (2) Å
c = 16.739 (4) Å
β = 112.646 (5)°
V = 3932.7 (16) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 298 K
0.20 × 0.18 × 0.15 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
17685 measured reflections
4931 independent reflections
3008 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.159
S = 1.02
4931 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812021617/bt5910sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812021617/bt5910Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812021617/bt5910Isup3.cml

checkCIF report

Comment top

Indole derivatives exhibit anti-oxidant (Olgen & Coban, 2003), anti-bacterial and fungicidal (Joshi & Chand, 1982) activities. Against this background, the title compound was chosen for X-ray structure analysis (Fig. 1).

The phenyl rings C11—C16 and C19—C24 form dihedral angles with the indole ring system of 79.03 (5)° and 61.82 (4)°, respectively.

The sum of the bond angles around N1 [359.99 (3)°] indicates sp² hybridization.

No classical hydrogen bonds are found in the crystal structure.

Related literature top

For the biological activity of indole derivatives, see: Olgen & Coban (2003); Joshi & Chand (1982).

Experimental top

A mixture of di- p-tolylacetylene (3.0 mmol), 2-methyl indole (2.0 mmol), and indium bromide (0.2 mmol) in toluene (4 ml) was stirred at 110 oC for the 120 min t s time. After completion of the reaction as indicated by TLC, the reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, concentrated in vacuo, and purified by column chromatography on silica gel (Merck, 100–200 mesh) to afford a mixture of E and Z (>99%) isomers. These major isomers were separated by crystallization using ethyl acetate/petroleum ether.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

3-(1,2-Di-p-tolylvinyl)-2-methyl-1H-indole top

Crystal data top

C₂₅H₂₃N	F(000) = 1440
M_r = 337.44	D_x = 1.140 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4931 reflections
a = 25.684 (6) Å	θ = 1.7–28.5°
b = 9.911 (2) Å	µ = 0.07 mm⁻¹
c = 16.739 (4) Å	T = 298 K
β = 112.646 (5)°	Block, colourless
V = 3932.7 (16) Å³	0.20 × 0.18 × 0.15 mm
Z = 8

Data collection top

Bruker SMART APEXII area-detector diffractometer	3008 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.041
Graphite monochromator	θ_max = 28.5°, θ_min = 1.7°
ω and ϕ scans	h = −30→34
17685 measured reflections	k = −13→7
4931 independent reflections	l = −22→21

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0719P)² + 0.9275P] where P = (F_o² + 2F_c²)/3
4931 reflections	(Δ/σ)_max = 0.004
238 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₂₅H₂₃N	V = 3932.7 (16) Å³
M_r = 337.44	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 25.684 (6) Å	µ = 0.07 mm⁻¹
b = 9.911 (2) Å	T = 298 K
c = 16.739 (4) Å	0.20 × 0.18 × 0.15 mm
β = 112.646 (5)°

Data collection top

Bruker SMART APEXII area-detector diffractometer	3008 reflections with I > 2σ(I)
17685 measured reflections	R_int = 0.041
4931 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 1.02	Δρ_max = 0.18 e Å⁻³
4931 reflections	Δρ_min = −0.14 e Å⁻³
238 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.23355 (7)	0.99325 (17)	0.37403 (11)	0.0635 (4)
C2	0.25810 (8)	1.1152 (2)	0.40950 (14)	0.0822 (6)
H2	0.2939	1.1187	0.4532	0.099*
C3	0.22776 (9)	1.2299 (2)	0.37794 (15)	0.0880 (6)
H3	0.2432	1.3131	0.4007	0.106*
C4	0.17463 (9)	1.22525 (19)	0.31288 (14)	0.0805 (5)
H4	0.1550	1.3052	0.2927	0.097*
C5	0.15015 (7)	1.10443 (17)	0.27736 (11)	0.0634 (4)
H5	0.1145	1.1027	0.2331	0.076*
C6	0.17940 (6)	0.98494 (15)	0.30850 (10)	0.0515 (4)
C7	0.16701 (6)	0.84417 (15)	0.29109 (10)	0.0515 (4)
C8	0.21325 (6)	0.77376 (17)	0.34289 (11)	0.0633 (4)
C9	0.22490 (9)	0.6260 (2)	0.35031 (16)	0.0933 (7)
H9A	0.1921	0.5782	0.3126	0.140*
H9B	0.2339	0.5977	0.4090	0.140*
H9C	0.2562	0.6069	0.3341	0.140*
C10	0.11288 (6)	0.78539 (15)	0.23107 (9)	0.0505 (3)
C11	0.09375 (6)	0.81897 (15)	0.13777 (9)	0.0504 (3)
C12	0.03693 (6)	0.81403 (17)	0.08275 (10)	0.0597 (4)
H12	0.0100	0.7934	0.1054	0.072*
C13	0.02008 (7)	0.83903 (18)	−0.00419 (10)	0.0634 (4)
H13	−0.0181	0.8348	−0.0391	0.076*
C14	0.05803 (7)	0.87039 (16)	−0.04178 (10)	0.0596 (4)
C15	0.11407 (7)	0.87811 (17)	0.01237 (11)	0.0625 (4)
H15	0.1407	0.8999	−0.0106	0.075*
C16	0.13152 (6)	0.85409 (16)	0.10024 (10)	0.0595 (4)
H16	0.1696	0.8617	0.1352	0.071*
C17	0.03825 (9)	0.8940 (2)	−0.13756 (12)	0.0831 (6)
H17A	0.0121	0.8244	−0.1679	0.125*
H17B	0.0700	0.8925	−0.1543	0.125*
H17C	0.0199	0.9802	−0.1517	0.125*
C18	0.08264 (6)	0.70194 (16)	0.25982 (10)	0.0565 (4)
H18	0.0523	0.6599	0.2169	0.068*
C19	0.09043 (6)	0.66727 (15)	0.34913 (10)	0.0528 (4)
C20	0.11046 (6)	0.75841 (15)	0.41800 (10)	0.0543 (4)
H20	0.1225	0.8435	0.4090	0.065*
C21	0.11272 (6)	0.72415 (17)	0.49952 (10)	0.0590 (4)
H21	0.1254	0.7874	0.5439	0.071*
C22	0.09638 (7)	0.59720 (19)	0.51636 (11)	0.0676 (5)
C23	0.07698 (9)	0.50732 (18)	0.44865 (13)	0.0774 (5)
H23	0.0658	0.4216	0.4582	0.093*
C24	0.07365 (7)	0.54136 (17)	0.36668 (12)	0.0682 (5)
H24	0.0598	0.4784	0.3223	0.082*
C25	0.09838 (12)	0.5605 (3)	0.60507 (14)	0.1054 (8)
H25A	0.0689	0.4971	0.5994	0.158*
H25B	0.0932	0.6403	0.6337	0.158*
H25C	0.1343	0.5208	0.6385	0.158*
N1	0.25296 (6)	0.86401 (15)	0.39323 (10)	0.0757 (4)
H1	0.2854	0.8423	0.4314	0.091*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0462 (8)	0.0636 (11)	0.0714 (11)	−0.0050 (7)	0.0125 (8)	−0.0026 (8)
C2	0.0596 (10)	0.0781 (13)	0.0916 (14)	−0.0180 (10)	0.0099 (10)	−0.0150 (11)
C3	0.0817 (13)	0.0645 (12)	0.1094 (16)	−0.0190 (10)	0.0276 (12)	−0.0165 (11)
C4	0.0811 (13)	0.0534 (10)	0.1020 (15)	−0.0002 (9)	0.0296 (11)	0.0019 (10)
C5	0.0550 (9)	0.0580 (10)	0.0717 (11)	0.0009 (7)	0.0182 (8)	0.0045 (8)
C6	0.0427 (7)	0.0534 (9)	0.0565 (8)	−0.0040 (6)	0.0171 (6)	0.0002 (7)
C7	0.0410 (7)	0.0523 (8)	0.0582 (9)	−0.0013 (6)	0.0160 (6)	−0.0001 (7)
C8	0.0474 (8)	0.0578 (10)	0.0757 (11)	0.0028 (7)	0.0137 (8)	0.0006 (8)
C9	0.0737 (12)	0.0647 (12)	0.1225 (18)	0.0173 (10)	0.0170 (12)	0.0056 (11)
C10	0.0429 (7)	0.0502 (8)	0.0553 (8)	0.0000 (6)	0.0156 (6)	−0.0034 (7)
C11	0.0458 (7)	0.0480 (8)	0.0558 (9)	0.0010 (6)	0.0177 (7)	−0.0023 (7)
C12	0.0464 (8)	0.0695 (10)	0.0618 (10)	−0.0015 (7)	0.0193 (7)	0.0032 (8)
C13	0.0464 (8)	0.0732 (11)	0.0616 (10)	−0.0019 (8)	0.0110 (7)	0.0007 (8)
C14	0.0624 (9)	0.0567 (9)	0.0572 (9)	−0.0003 (7)	0.0203 (8)	−0.0041 (7)
C15	0.0579 (9)	0.0693 (11)	0.0655 (10)	−0.0033 (8)	0.0295 (8)	−0.0004 (8)
C16	0.0451 (8)	0.0663 (10)	0.0631 (10)	−0.0035 (7)	0.0162 (7)	−0.0028 (8)
C17	0.0852 (13)	0.1020 (15)	0.0579 (11)	−0.0040 (11)	0.0230 (10)	0.0002 (10)
C18	0.0494 (8)	0.0578 (9)	0.0570 (9)	−0.0073 (7)	0.0147 (7)	−0.0072 (7)
C19	0.0450 (8)	0.0514 (8)	0.0585 (9)	−0.0012 (6)	0.0160 (7)	0.0020 (7)
C20	0.0488 (8)	0.0496 (8)	0.0610 (9)	−0.0002 (6)	0.0173 (7)	0.0024 (7)
C21	0.0514 (8)	0.0613 (10)	0.0563 (9)	0.0053 (7)	0.0121 (7)	0.0024 (7)
C22	0.0667 (10)	0.0669 (11)	0.0645 (11)	0.0082 (8)	0.0202 (8)	0.0165 (9)
C23	0.0913 (13)	0.0547 (10)	0.0850 (13)	−0.0062 (9)	0.0326 (11)	0.0148 (9)
C24	0.0755 (11)	0.0527 (10)	0.0722 (11)	−0.0104 (8)	0.0239 (9)	−0.0031 (8)
C25	0.136 (2)	0.1029 (17)	0.0779 (14)	0.0039 (15)	0.0424 (14)	0.0278 (12)
N1	0.0441 (7)	0.0726 (10)	0.0869 (11)	0.0043 (7)	−0.0010 (7)	0.0016 (8)

Geometric parameters (Å, º) top

C1—N1	1.367 (2)	C13—H13	0.9300
C1—C2	1.387 (2)	C14—C15	1.376 (2)
C1—C6	1.403 (2)	C14—C17	1.502 (2)
C2—C3	1.364 (3)	C15—C16	1.383 (2)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.380 (3)	C16—H16	0.9300
C3—H3	0.9300	C17—H17A	0.9600
C4—C5	1.377 (2)	C17—H17B	0.9600
C4—H4	0.9300	C17—H17C	0.9600
C5—C6	1.392 (2)	C18—C19	1.470 (2)
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.436 (2)	C19—C24	1.388 (2)
C7—C8	1.362 (2)	C19—C20	1.398 (2)
C7—C10	1.485 (2)	C20—C21	1.386 (2)
C8—N1	1.374 (2)	C20—H20	0.9300
C8—C9	1.491 (3)	C21—C22	1.389 (2)
C9—H9A	0.9600	C21—H21	0.9300
C9—H9B	0.9600	C22—C23	1.375 (3)
C9—H9C	0.9600	C22—C25	1.510 (3)
C10—C18	1.344 (2)	C23—C24	1.383 (2)
C10—C11	1.483 (2)	C23—H23	0.9300
C11—C16	1.388 (2)	C24—H24	0.9300
C11—C12	1.395 (2)	C25—H25A	0.9600
C12—C13	1.372 (2)	C25—H25B	0.9600
C12—H12	0.9300	C25—H25C	0.9600
C13—C14	1.384 (2)	N1—H1	0.8600

N1—C1—C2	130.67 (16)	C13—C14—C17	120.83 (15)
N1—C1—C6	106.90 (14)	C14—C15—C16	121.29 (15)
C2—C1—C6	122.41 (16)	C14—C15—H15	119.4
C3—C2—C1	117.58 (17)	C16—C15—H15	119.4
C3—C2—H2	121.2	C15—C16—C11	121.84 (14)
C1—C2—H2	121.2	C15—C16—H16	119.1
C2—C3—C4	121.40 (18)	C11—C16—H16	119.1
C2—C3—H3	119.3	C14—C17—H17A	109.5
C4—C3—H3	119.3	C14—C17—H17B	109.5
C5—C4—C3	121.23 (18)	H17A—C17—H17B	109.5
C5—C4—H4	119.4	C14—C17—H17C	109.5
C3—C4—H4	119.4	H17A—C17—H17C	109.5
C4—C5—C6	119.17 (16)	H17B—C17—H17C	109.5
C4—C5—H5	120.4	C10—C18—C19	129.53 (14)
C6—C5—H5	120.4	C10—C18—H18	115.2
C5—C6—C1	118.19 (14)	C19—C18—H18	115.2
C5—C6—C7	134.86 (14)	C24—C19—C20	116.88 (15)
C1—C6—C7	106.93 (13)	C24—C19—C18	119.56 (14)
C8—C7—C6	107.33 (13)	C20—C19—C18	123.40 (14)
C8—C7—C10	126.10 (14)	C21—C20—C19	121.10 (15)
C6—C7—C10	126.51 (13)	C21—C20—H20	119.4
C7—C8—N1	108.43 (15)	C19—C20—H20	119.4
C7—C8—C9	130.86 (16)	C20—C21—C22	121.36 (16)
N1—C8—C9	120.72 (15)	C20—C21—H21	119.3
C8—C9—H9A	109.5	C22—C21—H21	119.3
C8—C9—H9B	109.5	C23—C22—C21	117.47 (16)
H9A—C9—H9B	109.5	C23—C22—C25	121.24 (18)
C8—C9—H9C	109.5	C21—C22—C25	121.27 (18)
H9A—C9—H9C	109.5	C22—C23—C24	121.59 (17)
H9B—C9—H9C	109.5	C22—C23—H23	119.2
C18—C10—C11	120.81 (13)	C24—C23—H23	119.2
C18—C10—C7	121.24 (14)	C23—C24—C19	121.57 (16)
C11—C10—C7	117.94 (12)	C23—C24—H24	119.2
C16—C11—C12	116.48 (14)	C19—C24—H24	119.2
C16—C11—C10	121.80 (13)	C22—C25—H25A	109.5
C12—C11—C10	121.71 (13)	C22—C25—H25B	109.5
C13—C12—C11	121.11 (14)	H25A—C25—H25B	109.5
C13—C12—H12	119.4	C22—C25—H25C	109.5
C11—C12—H12	119.4	H25A—C25—H25C	109.5
C12—C13—C14	122.23 (14)	H25B—C25—H25C	109.5
C12—C13—H13	118.9	C1—N1—C8	110.39 (13)
C14—C13—H13	118.9	C1—N1—H1	124.8
C15—C14—C13	117.00 (15)	C8—N1—H1	124.8
C15—C14—C17	122.17 (15)

N1—C1—C2—C3	−178.7 (2)	C10—C11—C12—C13	−176.84 (15)
C6—C1—C2—C3	−0.5 (3)	C11—C12—C13—C14	−0.1 (3)
C1—C2—C3—C4	−0.2 (3)	C12—C13—C14—C15	−1.2 (3)
C2—C3—C4—C5	0.1 (3)	C12—C13—C14—C17	178.54 (17)
C3—C4—C5—C6	0.7 (3)	C13—C14—C15—C16	0.7 (2)
C4—C5—C6—C1	−1.4 (2)	C17—C14—C15—C16	−179.04 (16)
C4—C5—C6—C7	176.60 (17)	C14—C15—C16—C11	1.1 (3)
N1—C1—C6—C5	179.83 (14)	C12—C11—C16—C15	−2.3 (2)
C2—C1—C6—C5	1.3 (3)	C10—C11—C16—C15	176.34 (15)
N1—C1—C6—C7	1.32 (18)	C11—C10—C18—C19	−172.65 (14)
C2—C1—C6—C7	−177.21 (16)	C7—C10—C18—C19	8.8 (2)
C5—C6—C7—C8	179.97 (17)	C10—C18—C19—C24	−150.56 (17)
C1—C6—C7—C8	−1.89 (18)	C10—C18—C19—C20	34.2 (2)
C5—C6—C7—C10	−2.8 (3)	C24—C19—C20—C21	−0.7 (2)
C1—C6—C7—C10	175.31 (14)	C18—C19—C20—C21	174.69 (14)
C6—C7—C8—N1	1.72 (19)	C19—C20—C21—C22	1.4 (2)
C10—C7—C8—N1	−175.50 (14)	C20—C21—C22—C23	−1.0 (2)
C6—C7—C8—C9	−177.8 (2)	C20—C21—C22—C25	−179.43 (17)
C10—C7—C8—C9	5.0 (3)	C21—C22—C23—C24	−0.1 (3)
C8—C7—C10—C18	58.0 (2)	C25—C22—C23—C24	178.30 (19)
C6—C7—C10—C18	−118.71 (18)	C22—C23—C24—C19	0.9 (3)
C8—C7—C10—C11	−120.58 (17)	C20—C19—C24—C23	−0.5 (2)
C6—C7—C10—C11	62.7 (2)	C18—C19—C24—C23	−176.00 (16)
C18—C10—C11—C16	−152.49 (15)	C2—C1—N1—C8	178.08 (19)
C7—C10—C11—C16	26.1 (2)	C6—C1—N1—C8	−0.3 (2)
C18—C10—C11—C12	26.1 (2)	C7—C8—N1—C1	−0.9 (2)
C7—C10—C11—C12	−155.35 (14)	C9—C8—N1—C1	178.67 (18)
C16—C11—C12—C13	1.8 (2)

Experimental details

Crystal data
Chemical formula	C₂₅H₂₃N
M_r	337.44
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	25.684 (6), 9.911 (2), 16.739 (4)
β (°)	112.646 (5)
V (Å³)	3932.7 (16)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.20 × 0.18 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	17685, 4931, 3008
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.671

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.159, 1.02
No. of reflections	4931
No. of parameters	238
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.14

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Acknowledgements

The authors thank Dr Babu Varghese, SAIF, IIT–Madras, India, for the data collection.

References

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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